Pivaloyl chloride → N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2,2-dimethylpropanamide

HRID 1035770Notes

Reaction equation

HRID 1035770 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chloride2×HCID 67524192HCID 67524192, compound

Product 1

HCID 67524335N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 193 mg of 3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-amine and 0.14 cm3 of pivaloyl chloride in 5 cm3 of pyridine is stirred for 5 h at 20° C. 0.14 cm3 of pivaloyl chloride is again added and the mixture is left to stir overnight. The reaction medium obtained is concentrated to dryness under vacuum. The residue is washed with ethyl ether and pentane. The precipitate is taken up in a solution of ammonium chloride and then extracted with a 90/10 ethyl acetate/methanol mixture. The organic phase is evaporated to dryness. 157 mg of N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2,2-dimethylpropanamide are thus obtained in the form of a brown powder, the characteristics of which are as follows:

Workup

  1. waitthe mixture is left
  2. stirringto stir overnight
  3. customThe reaction medium obtained
  4. concentrationis concentrated to dryness under vacuum
  5. washThe residue is washed with ethyl ether and pentane
  6. extractionextracted with a 90/10 ethyl acetate/methanol mixture
  7. customThe organic phase is evaporated to dryness

Sources & evidence

ORD record
ord-c4956eb1958745a7b4de2fb0d587cae3
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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